Sulfamic Acid → 2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 716052Notes

Reaction equation

HRID 716052 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([CH:11]=[O:12])=[CH:9][N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:5]2=[N:6][CH:7]=1.S(=O)(=O)([OH:23])N.[O-]Cl=O.[Na+].OP([O-])(O)=O.[K+]>O1CCOCC1.O>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]([OH:23])=[O:12])=[CH:9][N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 578296122-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

Product 1

HCID 584385252-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidYield 67.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a 25 ml round bottom flask, 2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (0.1 g, 0.00028 mol) and sulphamic acid (0.163 g, 0.00168 mol) were taken in dioxane (1 ml) and water (0.1 ml). A solution of NaClO2 (0.032 g, 0.00036 mol) and KH2PO4 (0.458 g, 0.00336 mol) in water (0.9 ml) was added at 0° C. and the reaction mixture was stirred at room temperature for 2 hr. After completion of the reaction, the reaction mixture was partitioned between water and ethyl acetate. The combined organics were washed with brine solution. The organic layer was separated and dried over sodium sulphate, concentrated to give 0.07 g of 2-bromo-5-((2-(trimethylsilyl)ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid which was used as such in next step.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. washThe combined organics were washed with brine solution
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-26ae082a1ff74d53b104d83b1202c614
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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